Oprah, kobe Bryant, Sharon osbor Osborne. They're all rich, but all have family trying to turn them into personal atms. Following the money trail of family moochers. Reporter: In pop culture, freeloading friends and relatives make for comedy magic, such as "Seinfeld's" Kramer. His whole life is a fantasy camp. Do nothing, fall ass-backwards into money, mooch food off your neighbors. Reporter: Not that there's anything wrong with that. But high-earning celebrities can get beseiged in real life by gimme gimme gimme moochers, especially family. And they don't just ask for a fridge, they want the whole house. Just ask Oprah Winfrey. When I was making $22,000 a year, people always needed $50. Then when I moved to $50,000 a year, everybody needs like $500. Now, nobody needs anything less than $50,000. Reporter: Who could forget this epic giveaway? You get a car! And you get a car! And you get a car! But when it comes to an ex-stepmother, even the famously generous Oprah has her be-your-best-self limits. Barbara Winfrey married Oprah's father, Vernon, and lived with him in this $1.4 million house that Oprah bought them. When they divorced, Oprah asked her to move out. You're a billionaire. God has blessed you to be a billionaire, and this is what you do? Reporter: Oprah, according to a spokesperson, offered to split the proceeds from the sale of the house or to buy her a more modest home. Reportedly, what she asked in exchange was that Barbara Winfrey sign a confidentiality agreement. But for this ex-stepmom, talk isn't that cheap. She knows I know the story. I know the story. And to set me out now, why shouldn't I just tell my story? Reporter: Here's a true story. Family can be more avid than anyone to raid the bank of a big name. Why do you think relatives of the famous are so eager for their money? It's tough. Because they're family. It's like you become royalty. Reporter: Brett Erlich expertly dices and slices the zeitgeist for the youtube show "Pop trigger" and has his own solution for the money-minded moochtastic. There should be a celebrity family union and they should negotiate different rates. Much in the same way like your agent gets 10%, maybe your mom gets a house, your sister gets a car and your cousins get fancy sneakers, and that's it. And we cut them off after that. Reporter: He might agree. These days, shia labeouf can be seen trysting the night away in "Nymphomaniac" or putting this "I am not famous" bag over his head. Cool, bro. Still, he was flush enough to loan an uncle a sack of cash -- $800,000 worth. After the loan wasn't repaid, shia came here, to this courthouse, to make his debtor say uncle. Author of "Celebrity, inc.", Jo piazza knows all about stars and their money. The uncle said that he had been giving shia and his mother, who is a single mom, financial support for years and that he never asked for repayment, so he didn't really expect that he had to repay the loan that shia gave him. I want to help you, but I'm not some alien ambassador. I'm just a Normal kid with problems. Reporter: A reported $5 million salary for "Transformers: Revenge of the fallen?" No problem. An $800,000 relative misunderstanding? Big problem. Shia did not expect that moneould be a gift. Reporter: But for a celebrity, flinging an alleged family moocher off the money train can lead to some highly unflattering consequences, so Sharon Osborne's declared about her brother. All he does is earn money from selling lies and foul things about myself and my family. He sold five different stories on me to the british press. Reporter: Why? Because the pair had a falling out after their father's death, and she pulled the financial plug after years of supporting her brother, whom we were unable to reach for comment. All I did was give him money. I employed him. I gave him whatever he wanted. ,A Reporter: Fresh-faced and effortlessly glamorous, "Gossip girl" Leighton Meester wanted to pay for her ill young brother's healthcare needs. Only, the actress claimed, the $7,500 a month she sent his way healed her mother's money cravings instead and was allegedly used for, among other things, mom's cosmetic surgery. When the actress went to court, a judge put a new face on things, ruling that constance Meester had zero right to mooch off her daughter's dough. Everybody seems to think that they did a little something to contribute to that person becoming so rich and famous. There's a little sense of entitlement. And therefore, they think they deserve it. There is nothing like a good lie. You lie, the person accepts it completely and you walk away going, "Lie accomplished." Reporter: Dane cook could do a less-than-hilarious monologue about his half-brother, who wholeheartedly lived off his earnings, embezzling millions over a four-year period while serving as cook's business manager. That half-brother was sentenced to no-kidding time in the state pen. Reporter: Some even try cashing in on precious rewards for a job well done. Basketball star kobe Bryant stepped in days before his mother was to have auctioned off close to 100 items from his career. She did wind up selling a couple of kobe's high school Jerseys, a 2000 NBA all-star ring and an additional championship ring he'd previously given to his father. They settled their differences, his parents apologized publicly, but before that kobe tweeted out feelings that others in the public eye can relate to. "When U give give and they take take take at wat point do U draw a line in the sand?" More importantly, how do you stop your mother from selling that sand? Carpet,

This transcript has been automatically generated and may not be 100% accurate.

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